Annapolis Homes for Sale

Annapolis Homes for Sale

Welcome to Annapolis, Maryland, a city steeped in rich history and vibrant culture, nestled along the picturesque Chesapeake Bay. Known as the sailing capital of the U.S., Annapolis boasts stunning waterfront views, charming cobblestone streets, and a lively downtown area that perfectly blends historic charm with modern amenities. The city is home to the United States Naval Academy and offers a unique mix of maritime heritage and contemporary living.

In this enchanting subdivision, you’ll find a diverse array of homes for sale, catering to various lifestyles and preferences. Whether you’re searching for a cozy bungalow, a spacious family home, or a luxurious waterfront property, Annapolis has something to suit every taste. Many of these homes feature beautiful architectural designs, modern upgrades, and ample outdoor spaces, perfect for enjoying the delightful Maryland weather.

Living in Annapolis means embracing a lifestyle filled with outdoor activities, from sailing and fishing to hiking and biking along scenic trails. The community is also rich in arts and culture, with numerous galleries, theaters, and annual festivals that celebrate the local heritage. Plus, with its proximity to Washington D.C. and Baltimore, residents enjoy easy access to urban conveniences while still relishing the tranquility of a charming coastal town.

Explore the homes for sale in Annapolis and discover your dream residence in this captivating city. Experience the perfect blend of history, community, and natural beauty that makes Annapolis a truly exceptional place to call home.

Newest Annapolis Homes for Sale

1925 Fairfax Rd, Annapolis
$700,000
5 Beds ⋅ 3 Baths
Stunning, updated home on a spacious .6-acre lot located just 2 miles from historic downtown Annapolis. The main level boasts beautifully refinished hardwood floors, updated eat-in kitchen, and a separate dining room. The bright living room with a wood-burning fireplace flows effortlessly toward outdoor living, featuring a spacious screened-in porch that exits to a large back deck. A desirable main-floor bedroom with a full ensuite bathroom offers ultimate convenience. Upstairs, you will find three additional hardwood-floored bedrooms sharing a tastefully updated full bathroom. The versatile basement provides a flexible space perfect for a rec room or fifth bedroom, complete with a full bath, laundry, and ample storage. The expansive, private backyard completes this property with a detached one-car garage and an additional separate storage shed.

1925 Fairfax Rd, Annapolis

Listing courtesy of RE/MAX Leading Edge. Contact:

1952 Forest Dr, Annapolis
$435,000
3 Beds ⋅ 2 Baths
Beautiful Move-In Ready Home with Spacious Fenced Backyard! Welcome to this clean, beautiful, and well-maintained 3-bedroom, 2-full-bath home, offering comfortable living spaces and everything you need to move right in and enjoy. The inviting kitchen features beautiful granite countertops and plenty of space for cooking and entertaining. The spacious family room is highlighted by a warm, attractive fireplace, creating the perfect setting for relaxing with family and friends. Step outside and discover the large, fully fenced backyard, offering plenty of room for outdoor entertaining, gardening, recreation, or simply enjoying your own private outdoor space. With its desirable layout, attractive finishes, spacious backyard, and move-in-ready condition, this home is a wonderful opportunity for anyone looking for comfort, convenience, and a place to call home. All information must confirm by the buyer. Don’t miss the opportunity to see this beautiful home! Schedule your showing today.

1952 Forest Dr, Annapolis

Listing courtesy of Blufin Realty, LLC.. Contact:

208 Admiral Dr, Annapolis
$325,000
2 Beds ⋅ 1 Baths

208 Admiral Dr, Annapolis

Listing courtesy of RE/MAX One. Contact:

146 Duke Of Gloucester St, Annapolis
$1,950,000
4 Beds ⋅ 4 Baths
Price improvement!!! Welcome to 146 Duke of Gloucester Street! As you approach the home, a welcoming front porch will greet you, offering a place to sit and take in all that Annapolis has to offer. Nestled in the heart of historic Annapolis, this beautifully appointed 4-bedroom, 3.5-bath residence seamlessly blends timeless charm with modern sophistication. Rich in character and thoughtfully updated throughout, this exceptional home offers an inviting open-concept main level designed for both comfortable living and effortless entertaining. Step inside to discover sun-filled living and dining spaces anchored by a stunning exposed brick fireplace that adds warmth and historic appeal. The modern kitchen is a true centerpiece, featuring stylish finishes, ample cabinetry, and a functional layout perfect for everyday living and hosting guests alike. The second level features three spacious bedrooms filled with natural light from oversized windows, generous closet space, and two beautifully appointed full bathrooms, creating comfortable accommodations for family and guests alike. Occupying the entire third floor, the expansive primary suite serves as a private retreat complete with a luxurious spa-inspired bath designed for relaxation and rejuvenation. Outside, enjoy a charming backyard—an ideal setting for outdoor dining, gardening, or simply unwinding in your own private oasis. Perfectly situated just moments from the waterfront, renowned restaurants, boutique shopping, and the rich history of downtown Annapolis, this home offers a rare opportunity to experience historic living with all the comforts of modern design.

146 Duke Of Gloucester St, Annapolis

Listing courtesy of Douglas Realty LLC. Contact:

220 West St, Annapolis
$849,900
3 Beds ⋅ 2 Baths
Welcome to 220 West Street in Annapolis, Maryland. A rare, fully gut-renovated detached property located in the heart of the Downtown Arts District at a row home's price, offering exceptional flexibility with mixed-use zoning that allows for both residential and commercial use. Completed in 2024, this property has been completely transformed from top to bottom. Every major system and finish has been replaced, delivering a true turnkey opportunity for buyers seeking lifestyle, investment potential, or business use in one of the most walkable and desirable areas in Annapolis. Unlike the majority of Downtown Annapolis properties, this is a fully detached home, not a rowhome or townhouse, providing enhanced privacy, natural light, and a more versatile footprint. The extensive renovation includes a brand new roof, all new electrical and plumbing systems, a new high-efficiency mini-split HVAC system, redesigned floor plan, new flooring throughout, updated lighting, and fully rebuilt kitchen and bathrooms. The outdoor spaces have been completely upgraded with a new deck, new brick patio pavers, new fencing, and ambient lighting that creates a warm and inviting atmosphere for evening entertaining. Inside, the home features a bright two-story entry foyer and a professionally curated interior design that blends modern comfort with intentional functionality. With three bedrooms and two full bathrooms, the layout is flexible enough to support full-time living, guest accommodations, workspace needs, or commercial adaptation. The main-level primary suite opens directly to a private brick patio, while the second bedroom features access to a rear deck overlooking the fully fenced yard. These indoor-outdoor connections are rarely found in Downtown Annapolis and significantly enhance livability. The kitchen has been completely reimagined with new cabinetry, countertops, and appliances, designed to support both daily living and entertaining. The open dining area comfortably accommodates gatherings, reinforcing the home’s versatility. Adding even more value, this property is being sold fully furnished. Every piece has been professionally selected, allowing the next owner to move in immediately, operate as a short-term rental, or transition into a commercial or mixed-use setup with minimal effort. Historically, this property has served multiple purposes, including a furniture store, office space, and duplex residence, highlighting the true flexibility and long-term value of its mixed-use zoning designation. Step outside into a fully fenced private yard featuring a brick patio, outdoor dining area, lounge seating, and ambient lighting, creating a unique urban retreat just steps from the energy of Downtown Annapolis. Located just moments from restaurants, shops, nightlife, City Dock, the Maryland State House, and the U.S. Naval Academy, this property offers unmatched walkability and access. With convenient proximity to Baltimore, Washington D.C., and BWI Airport, it is equally appealing for commuters, investors, and second-home buyers. This is more than a home. It is a rare, fully renovated, detached mixed-use opportunity in Downtown Annapolis where lifestyle, flexibility, and long-term value align.

220 West St, Annapolis

Listing courtesy of Keller Williams Realty Centre. Contact:

721 Fairway Dr, Annapolis
$567,000
3 Beds ⋅ 3 Baths
Elegant brick and siding split-foyer residence offering 3 bedrooms and 3 renovated full bathrooms on a beautifully sized 0.21-acre lot. The thoughtfully designed upper level features a sun-filled living room, formal dining area, well-appointed brand new kitchen with new appliances, and seamless access to the rear deck—perfect for refined indoor-outdoor living. Two bedrooms and two full baths complete the main level. The lower level is highlighted by a bedroom with a generously renovated full bathroom, providing an ideal owner’s retreat or guest quarters, along with a spacious family/recreation room, laundry area, and mechanical room. Luxury vinyl flooring extends throughout both levels, complemented by windows in excellent condition. Major updates include the roof and new outdoor HVAC system. Serviced by well and public sewer. A well-maintained home offering comfort, privacy, and timeless appeal.

721 Fairway Dr, Annapolis

Listing courtesy of KW Metro Center. Contact:

9 Shipwright St, Annapolis
$3,495,000
3 Beds ⋅ 3 Baths
Quintessential downtown Annapolis waterfront home on the sparkling waters of Spa Creek! This amazing property combines the best of both worlds; the charming historic feel of a downtown Annapolis home with the premier waterfront lifestyle that every resident is looking for. Nestled on a quiet street, this home is the perfect size for an easy to own, lock up and go property. With 3 bedrooms and 2.5 baths it has all the elements needed to enjoy life to the fullest; either as the perfect weekend retreat or permanent residence. The Annapolis area and the surrounding waterways are sure to entertain in every season. The upper level of the home is dedicated to the spacious Primary suite with unique sitting area and expansive roof deck. Take in panoramic views of Spa Creek, Annapolis Harbor and Eastport. An unparalleled vantage point for sunrise coffee or sunset cocktails. The main level offers multiple cozy gathering areas including a formal living room with fireplace, home office and light filled gourmet kitchen with dining area. The kitchen area flows effortlessly into the dining area and out onto the rear deck overlooking Spa Creek. Perfect for gathers of all sizes and dining al fresco. The lower level provides an ideal retreat for family or guests with 2 spacious bedroom a full bath and a cozy family room with fireplace. Head out to the charming covered patio to read a book or sip your evening cocktail or venture out on the water from the private pier. The amazing location is walkable to everything Annapolis has to offer and Spa Creek provides quick access to the Chesapeake Bay and beyond. Welcome Home!

9 Shipwright St, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

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